Welcome to LookChem.com Sign In|Join Free

CAS

  • or

108-28-1

Post Buying Request

108-28-1 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

108-28-1 Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 2332, 1955 DOI: 10.1021/ja01613a092

Check Digit Verification of cas no

The CAS Registry Mumber 108-28-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 108-28:
(5*1)+(4*0)+(3*8)+(2*2)+(1*8)=41
41 % 10 = 1
So 108-28-1 is a valid CAS Registry Number.
InChI:InChI=1/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2

108-28-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name protoanemonin

1.2 Other means of identification

Product number -
Other names 5-methylidenefuran-2-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:108-28-1 SDS

108-28-1Synthetic route

5-hydroxy-5-methyl-2(5H)-furanone
14300-71-1

5-hydroxy-5-methyl-2(5H)-furanone

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform at 10 - 15℃; for 2h;82%
With trifluorormethanesulfonic acid In chloroform-d1 for 1.5h; Molecular sieve;
3,5-di-O-p-toluoyl-2-deoxy-D-ribono-1,4-lactone
53009-05-5

3,5-di-O-p-toluoyl-2-deoxy-D-ribono-1,4-lactone

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;80%
γ-hydroxymethyl-α,β-butenolide
10374-60-4

γ-hydroxymethyl-α,β-butenolide

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With sodium acetate Heating;60%
penta-3,4-dienoic acid
60053-24-9

penta-3,4-dienoic acid

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With iodine; sodium hydrogencarbonate; potassium iodide In water; acetonitrile 1.) 0 deg C, in the dark; 2.) 25 deg C, 3 d;57%
With iodine; sodium hydrogencarbonate; potassium iodide In water; acetonitrile 1.) 0 deg C, in the dark; 2.) 25 deg C, 3 d; various β-allenic acid investigated;57%
With potassium carbonate; copper dichloride; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 70℃; for 12h;31 % Spectr.
2-methylfuran
534-22-5

2-methylfuran

A

protoanemonin
108-28-1

protoanemonin

B

furfural
98-01-1

furfural

C

maleic anhydride
108-31-6

maleic anhydride

Conditions
ConditionsYield
With air; V-Mo-O catalyst on corundizium support at 350℃; for 0.000138889h; Product distribution; var. V:Mo ratios;A 43%
B 2%
C 24%
With air; vanadium-molybdenum oxide (V:Mo 3:1) oncorundizium support at 350℃; for 0.000138889h;A 43%
B 2%
C 24%
5-methyl-2-furanone
591-12-8

5-methyl-2-furanone

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
Stage #1: 5-methyl-2-furanone With bromine In tetrachloromethane at 0℃; for 1h;
Stage #2: With quinoline In benzene at 0 - 20℃; for 5h;
37%
(Z)-3-iodoprop-2-enoic acid
6214-35-3

(Z)-3-iodoprop-2-enoic acid

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With copper(l) iodide; palladium 10% on activated carbon; triethylamine; triphenylphosphine In 1,4-dioxane at 25 - 80℃; for 3.5h; Inert atmosphere; regioselective reaction;15%
5-(acetyloxy)-5-methyl-2(5H)-furanone
74982-59-5

5-(acetyloxy)-5-methyl-2(5H)-furanone

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With acetic anhydride; acetic acid
With sulfuric acid; acetic anhydride; acetic acid
With sulfuric acid In acetic anhydride; acetic acid at 80℃;
pent-2t-en-4-ynoic acid
68267-52-7

pent-2t-en-4-ynoic acid

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With hydrogen bromide; acetic acid
4-oxo-2-pentenoic acid
4743-82-2

4-oxo-2-pentenoic acid

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride; acetic acid
5-methyl-2-furanone
591-12-8

5-methyl-2-furanone

A

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With selenium(IV) oxide In 1,4-dioxane for 6h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
5-methyl-2-furanone
591-12-8

5-methyl-2-furanone

A

protoanemonin
108-28-1

protoanemonin

B

5-bromo-5-methyloxol-3-en-2-one
72137-30-5

5-bromo-5-methyloxol-3-en-2-one

C

4-bromo-5-methyloxol-4-en-2-one
85846-70-4

4-bromo-5-methyloxol-4-en-2-one

r-4,t-5-dibromo-c-5-methyloxolan-2-one
1424-35-7, 85846-69-1, 123694-21-3, 123694-22-4

r-4,t-5-dibromo-c-5-methyloxolan-2-one

Conditions
ConditionsYield
With N-Bromosuccinimide; sodium hydrogencarbonate; calcium oxide In tetrachloromethane for 28h; Ambient temperature; Irradiation; Yield given. Further byproducts given. Yields of byproduct given;
2-Methyl-5-tert-butylfuran
15146-95-9

2-Methyl-5-tert-butylfuran

A

furan
110-00-9

furan

B

2-methylfuran
534-22-5

2-methylfuran

C

protoanemonin
108-28-1

protoanemonin

D

furfural
98-01-1

furfural

E

maleic anhydride
108-31-6

maleic anhydride

F

5-(tert-butyl)furan-2-carbaldehyde
64122-20-9

5-(tert-butyl)furan-2-carbaldehyde

Conditions
ConditionsYield
With oxygen; vanadia; molybdenum(VI) oxide; silver(l) oxide Product distribution;
Trimethyl(5-methyl-2-furyl)silane
13271-75-5

Trimethyl(5-methyl-2-furyl)silane

A

furan
110-00-9

furan

B

2-methylfuran
534-22-5

2-methylfuran

C

protoanemonin
108-28-1

protoanemonin

D

furfural
98-01-1

furfural

E

maleic anhydride
108-31-6

maleic anhydride

F

(5-trimethylsilanyl)furan-2-carbaldehyde
13529-06-1

(5-trimethylsilanyl)furan-2-carbaldehyde

Conditions
ConditionsYield
With oxygen; vanadia; molybdenum(VI) oxide; silver(l) oxide Product distribution;
N-(1-deoxy-D-fructos-1-yl)-β-alanine
37721-43-0

N-(1-deoxy-D-fructos-1-yl)-β-alanine

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
at 195℃; for 0.25h; Product distribution; pyrolysis (various times and temperatures);
Mechanism; (14)C labelled at 1,2 and 6 positions (pyrolysis);
Conditions
ConditionsYield
at 280℃; for 0.25h; Mechanism; pyrolysis;
N-(1-deoxy-D-fructos-1-yl)-L-glycine
4429-05-4

N-(1-deoxy-D-fructos-1-yl)-L-glycine

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
at 195℃; for 0.25h; Product distribution; pyrolysis (various times and temperatures);
levulinic acid
123-76-2

levulinic acid

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
at 280℃; for 0.25h; Mechanism; pyrolysis;
Multi-step reaction with 2 steps
1.1: 60 percent / H3PO4 / Heating
2.1: Br2 / CCl4 / 1 h / 0 °C
2.2: 37 percent / quinoline / benzene / 5 h / 0 - 20 °C
View Scheme
(3aR,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2-ethoxy-dihydro-furo[3,4-d][1,3]dioxol-4-one
116504-11-1, 116504-23-5

(3aR,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2-ethoxy-dihydro-furo[3,4-d][1,3]dioxol-4-one

A

protoanemonin
108-28-1

protoanemonin

B

5-(tert-Butyl-dimethyl-silanyloxymethyl)-3H-furan-2-one
116504-12-2

5-(tert-Butyl-dimethyl-silanyloxymethyl)-3H-furan-2-one

C

5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5H-furan-2-one
116561-10-5

5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5H-furan-2-one

Conditions
ConditionsYield
With trimellitic anhydride at 300 - 320℃; under 60 - 80 Torr; for 3h; Yield given;
(-)-(S)-5-iodomethyloxol-3-en-2-one
85694-08-2

(-)-(S)-5-iodomethyloxol-3-en-2-one

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With cyanide(1-) In dichloromethane
methyl (Z)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-propenoate
103773-19-9

methyl (Z)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-propenoate

A

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With selenium(IV) oxide In 1,4-dioxane for 6h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
(-)-(S)-5-methanesulfonyloxymethyloxol-3-en-2-one
85694-07-1

(-)-(S)-5-methanesulfonyloxymethyloxol-3-en-2-one

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With pyrrolide anion
(S)-(5-oxo-2,5-dihydrofuran-2-yl)methyl 4-methylbenzenesulfonate
85694-06-0

(S)-(5-oxo-2,5-dihydrofuran-2-yl)methyl 4-methylbenzenesulfonate

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With cyanide(1-) In dichloromethane
Multi-step reaction with 2 steps
1: 63 percent / NaI / acetone / 8 h / Heating
2: Ag2O / CH2Cl2
View Scheme
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

D-Ribono-1,4-lactone
5336-08-3

D-Ribono-1,4-lactone

A

protoanemonin
108-28-1

protoanemonin

B

(5S)-5-(hydroxymethyl)-5H-furan-2-one
78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions
ConditionsYield
1.) THF, reflux; 2.) 220 deg C, 18 Hgmm; Multistep reaction;
(-)-(S)-5-iodomethyloxol-3-en-2-one
85694-08-2

(-)-(S)-5-iodomethyloxol-3-en-2-one

butan-1-ol
71-36-3

butan-1-ol

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With silver(l) oxide In dichloromethane
α-angelicalactone

α-angelicalactone

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
With carbon disulfide; bromine Behandeln einer Loesung des Reaktionsprodukts in Benzol oder Aether in Chinolin;
γ-acetoxy-γ-methyl-Δα.β-crotonoactone

γ-acetoxy-γ-methyl-Δα.β-crotonoactone

protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
bei der trocknen Destillation;
5-(acetyloxy)-5-methyl-2(5H)-furanone
74982-59-5

5-(acetyloxy)-5-methyl-2(5H)-furanone

sulfuric acid
7664-93-9

sulfuric acid

acetic anhydride
108-24-7

acetic anhydride

acetic acid
64-19-7

acetic acid

protoanemonin
108-28-1

protoanemonin

(-)-ranunculin
644-69-9

(-)-ranunculin

aqueous sodium acetate solution

aqueous sodium acetate solution

protoanemonin
108-28-1

protoanemonin

protoanemonin
108-28-1

protoanemonin

potassium phenyltrifluoborate

potassium phenyltrifluoborate

4-phenyl-5-methylenedihydrofuran-2-one
126833-53-2

4-phenyl-5-methylenedihydrofuran-2-one

Conditions
ConditionsYield
With 2-methoxy-phenol; bis(1,5-cyclooctadiene)rhodium(I) hexafluorophosphate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In toluene at 110 - 115℃; for 20h;90%
protoanemonin
108-28-1

protoanemonin

buta-1,3-diene
106-99-0

buta-1,3-diene

1-oxaspiro<4.5>deca-3,7-dien-2-one
84477-25-8

1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions
ConditionsYield
With hydroquinone at 155℃; for 4h;85%
at 180℃;34%
protoanemonin
108-28-1

protoanemonin

2,3-dimethyl-buta-1,3-diene
513-81-5

2,3-dimethyl-buta-1,3-diene

7,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-2-one
126109-77-1

7,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions
ConditionsYield
With hydroquinone at 170℃; for 4h;81%
With hydroquinone at 162℃; for 4h;81%
protoanemonin
108-28-1

protoanemonin

trans-2-methyl-1,3-pentadiene
926-54-5

trans-2-methyl-1,3-pentadiene

6,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-2-one
126036-63-3

6,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions
ConditionsYield
With hydroquinone at 159℃; for 4h;80%
protoanemonin
108-28-1

protoanemonin

isoprene
78-79-5

isoprene

8-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one
126036-64-4

8-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions
ConditionsYield
With hydroquinone at 154℃; for 4h; Further byproducts given;75%
protoanemonin
108-28-1

protoanemonin

N-hydroxy-4-methoxy-benzenecarboximidoyl chloride
38435-51-7

N-hydroxy-4-methoxy-benzenecarboximidoyl chloride

3,3'-bis(p-anisyl)-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]

3,3'-bis(p-anisyl)-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]

Conditions
ConditionsYield
With triethylamine; hydroquinone In diethyl ether at 20℃;74%
protoanemonin
108-28-1

protoanemonin

1-methylbuta-1,3-diene
2004-70-8

1-methylbuta-1,3-diene

6-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one
126036-62-2

6-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions
ConditionsYield
With hydroquinone at 150℃; for 4h;72%
protoanemonin
108-28-1

protoanemonin

trans-2-methyl-1,3-pentadiene
926-54-5

trans-2-methyl-1,3-pentadiene

A

7,9-Dimethyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

7,9-Dimethyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

B

6,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-2-one
126036-63-3

6,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions
ConditionsYield
With hydroquinone at 150℃; for 4h;A n/a
B 70%
protoanemonin
108-28-1

protoanemonin

N-hydroxy-4-methylbenzenecarboximidoyl chloride
36288-37-6

N-hydroxy-4-methylbenzenecarboximidoyl chloride

3,3'-Di-p-tolyl-4,5-dihydro-[5,5']biisoxazolyl

3,3'-Di-p-tolyl-4,5-dihydro-[5,5']biisoxazolyl

Conditions
ConditionsYield
With triethylamine In toluene for 6h; Heating;70%
protoanemonin
108-28-1

protoanemonin

N-hydroxy-4-methylbenzenecarboximidoyl chloride
36288-37-6

N-hydroxy-4-methylbenzenecarboximidoyl chloride

3,3'-bis(p-tolyl)-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]
292605-27-7

3,3'-bis(p-tolyl)-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]

Conditions
ConditionsYield
With triethylamine; hydroquinone In diethyl ether at 20℃;69%
protoanemonin
108-28-1

protoanemonin

isoprene
78-79-5

isoprene

A

7-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one
126036-65-5

7-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

B

8-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one
126036-64-4

8-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions
ConditionsYield
With hydroquinone at 155℃; for 4h;A n/a
B 65%
aluminium trichloride In dichloromethane for 21h; Product distribution; Ambient temperature; also without catalyst, various dienes, other temp., time, solvent;
at 108℃; Kinetics; Thermodynamic data; energy barriers: Ep, Em; other temp.;
protoanemonin
108-28-1

protoanemonin

1-methylbuta-1,3-diene
2004-70-8

1-methylbuta-1,3-diene

A

9-Methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

9-Methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

B

6-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one
126036-62-2

6-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions
ConditionsYield
With hydroquinone at 150℃; for 4h;A n/a
B 64%
protoanemonin
108-28-1

protoanemonin

A

1,2-propanediene
463-49-0

1,2-propanediene

B

maleic anhydride
930-60-9

maleic anhydride

C

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
at 1100℃;A 10%
B 60%
C 25%
protoanemonin
108-28-1

protoanemonin

N-hydroxy-4-methoxy-benzenecarboximidoyl chloride
38435-51-7

N-hydroxy-4-methoxy-benzenecarboximidoyl chloride

3,3'-Bis-(4-methoxy-phenyl)-4,5-dihydro-[5,5']biisoxazolyl

3,3'-Bis-(4-methoxy-phenyl)-4,5-dihydro-[5,5']biisoxazolyl

Conditions
ConditionsYield
With triethylamine In toluene for 6h; Heating;60%
protoanemonin
108-28-1

protoanemonin

benzohydroximoyl chloride
698-16-8

benzohydroximoyl chloride

3,3'-diphenyl-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]
292605-26-6

3,3'-diphenyl-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]

Conditions
ConditionsYield
With triethylamine; hydroquinone In diethyl ether at 20℃;60%
protoanemonin
108-28-1

protoanemonin

C17H30N2O5Si
1426817-89-1

C17H30N2O5Si

C22H34O7Si

C22H34O7Si

Conditions
ConditionsYield
With rhodium(II) acetate dimer In toluene at 25℃;60%
protoanemonin
108-28-1

protoanemonin

tert-butyl 2-diazo-3,6-dioxoheptanoate
573692-80-5

tert-butyl 2-diazo-3,6-dioxoheptanoate

C16H20O6

C16H20O6

Conditions
ConditionsYield
With rhodium(II) acetate dimer In toluene at 25℃;59%
protoanemonin
108-28-1

protoanemonin

cyclohexa-1,3-diene
1165952-91-9

cyclohexa-1,3-diene

3-((1R*,2S*,4R*)-2-Hydroxybicyclo<2.2.2>oct-5-en-2-yl)propanoic acid 1,4-lactone
130619-40-8, 130696-40-1

3-((1R*,2S*,4R*)-2-Hydroxybicyclo<2.2.2>oct-5-en-2-yl)propanoic acid 1,4-lactone

3-((1R*,2R*,4R*)-2-Hydroxybicyclo<2.2.2>oct-5-en-2-yl)propanoic acid 1,4-lactone
130619-40-8, 130696-40-1

3-((1R*,2R*,4R*)-2-Hydroxybicyclo<2.2.2>oct-5-en-2-yl)propanoic acid 1,4-lactone

Conditions
ConditionsYield
In dichloromethane at 165℃; for 2h;A 54%
B 24%
protoanemonin
108-28-1

protoanemonin

Conditions
ConditionsYield
53%
protoanemonin
108-28-1

protoanemonin

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(1SR, 2RS, 4SR)-3-(2-hydroxybicyclo[2.2.1]hept-5-en-2-yl)prop-2-enoic acid lactone
130619-39-5, 130696-39-8

(1SR, 2RS, 4SR)-3-(2-hydroxybicyclo[2.2.1]hept-5-en-2-yl)prop-2-enoic acid lactone

(1SR, 2SR, 4SR)-3-(2-hydroxybicyclo[2.2.1]hept-5-en-2-yl)prop-2-enoic acid lactone
130619-39-5, 130696-39-8

(1SR, 2SR, 4SR)-3-(2-hydroxybicyclo[2.2.1]hept-5-en-2-yl)prop-2-enoic acid lactone

Conditions
ConditionsYield
In dichloromethane at 90℃; for 2h;A 22%
B 52%
In dichloromethane at 60℃; for 70.7h; Kinetics; Product distribution; reactions at different temperatures; reactions with cyclohexadiene at different temperatures;
In dichloromethane at 160℃; for 7.5h; Yield given. Yields of byproduct given;
In dichloromethane at 60℃; for 70.7h; Yield given. Yields of byproduct given;
protoanemonin
108-28-1

protoanemonin

N-phenyl-C-(4-nitrobenzoyl)nitrone
22269-68-7

N-phenyl-C-(4-nitrobenzoyl)nitrone

(3'RS;5,5'RS)-3'-(4-nitrobenzoyl)-2'-phenyl-2',3'-dihydrospiroisoxazolino[5':5]-(5H)-furan-2-one

(3'RS;5,5'RS)-3'-(4-nitrobenzoyl)-2'-phenyl-2',3'-dihydrospiroisoxazolino[5':5]-(5H)-furan-2-one

Conditions
ConditionsYield
With hydroquinone In ethyl acetate at 20℃; for 24h;52%
protoanemonin
108-28-1

protoanemonin

benzohydroximoyl chloride
698-16-8

benzohydroximoyl chloride

anemonin

anemonin

B

3,3'-diphenyl-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]
292605-26-6

3,3'-diphenyl-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]

C

2,5-dihydro-3'-phenylspiroisoxazolino-[5',5]furan-2-one
292605-22-2

2,5-dihydro-3'-phenylspiroisoxazolino-[5',5]furan-2-one

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 24h;A n/a
B 26%
C 51%
protoanemonin
108-28-1

protoanemonin

4-chlorobenzohydroximoyl chloride
28123-63-9

4-chlorobenzohydroximoyl chloride

3,3'-Bis-(4-chloro-phenyl)-4,5-dihydro-[5,5']biisoxazolyl

3,3'-Bis-(4-chloro-phenyl)-4,5-dihydro-[5,5']biisoxazolyl

Conditions
ConditionsYield
With triethylamine In toluene for 6h; Heating;50%
protoanemonin
108-28-1

protoanemonin

1-pyrroline N-oxide
24423-88-9

1-pyrroline N-oxide

(2RS,3a'SR)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

(2RS,3a'SR)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

(2RS,3a'RS)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

(2RS,3a'RS)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

(3RS,3aRS,8aSR,8bSR,3a'RS)-spiro[tetrahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-3(3aH),2'(3'H)-tetrahydropyrrolo[1,2-b]isoxazol]-1(8bH)-one

(3RS,3aRS,8aSR,8bSR,3a'RS)-spiro[tetrahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-3(3aH),2'(3'H)-tetrahydropyrrolo[1,2-b]isoxazol]-1(8bH)-one

(RS,RS)-1,7-dioxa-dispiro[4.0.4.2]dodeca-3,9-diene-2,8-dione
508-44-1

(RS,RS)-1,7-dioxa-dispiro[4.0.4.2]dodeca-3,9-diene-2,8-dione

Conditions
ConditionsYield
In chloroform at 70℃; for 4h; Further byproducts given;A 2%
B 50%
C 16 mg
D 15%
protoanemonin
108-28-1

protoanemonin

1-pyrroline N-oxide
24423-88-9

1-pyrroline N-oxide

(2RS,3a'RS)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

(2RS,3a'RS)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

(3RS,3aRS,8aRS,8bSR,3a'RS)-spiro[tetrahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-3(3aH),2'(3'H)-tetrahydropyrrolo[1,2-b]isoxazol]-1(8bH)-one

(3RS,3aRS,8aRS,8bSR,3a'RS)-spiro[tetrahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-3(3aH),2'(3'H)-tetrahydropyrrolo[1,2-b]isoxazol]-1(8bH)-one

(3RS,3aRS,8aSR,8bSR,3a'RS)-spiro[tetrahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-3(3aH),2'(3'H)-tetrahydropyrrolo[1,2-b]isoxazol]-1(8bH)-one

(3RS,3aRS,8aSR,8bSR,3a'RS)-spiro[tetrahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-3(3aH),2'(3'H)-tetrahydropyrrolo[1,2-b]isoxazol]-1(8bH)-one

(RS,RS)-1,7-dioxa-dispiro[4.0.4.2]dodeca-3,9-diene-2,8-dione
508-44-1

(RS,RS)-1,7-dioxa-dispiro[4.0.4.2]dodeca-3,9-diene-2,8-dione

Conditions
ConditionsYield
In chloroform at 70℃; for 4h; Yield given. Further byproducts given. Title compound not separated from byproducts;A 50%
B n/a
C 16 mg
D 15%
protoanemonin
108-28-1

protoanemonin

(2RS,3a'SR)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

(2RS,3a'SR)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

(2RS,3a'RS)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

(2RS,3a'RS)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

(3RS,3aRS,8aSR,8bSR,3a'RS)-spiro[tetrahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-3(3aH),2'(3'H)-tetrahydropyrrolo[1,2-b]isoxazol]-1(8bH)-one

(3RS,3aRS,8aSR,8bSR,3a'RS)-spiro[tetrahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-3(3aH),2'(3'H)-tetrahydropyrrolo[1,2-b]isoxazol]-1(8bH)-one

(RS,RS)-1,7-dioxa-dispiro[4.0.4.2]dodeca-3,9-diene-2,8-dione
508-44-1

(RS,RS)-1,7-dioxa-dispiro[4.0.4.2]dodeca-3,9-diene-2,8-dione

Conditions
ConditionsYield
With 1-pyrroline N-oxide In chloroform at 70℃; for 4h; Further byproducts given;A 2%
B 50%
C 16 mg
D 15%

108-28-1Relevant articles and documents

Deoxyribonolactone formation in photoirradiation of 5-bromouracil-containing oligonucleotides by direct C1′ hydrogen abstraction

Fujimoto, Kenzo,Ikeda, Yutaka,Ishihara, Shigenori,Saito, Isao

, p. 2243 - 2245 (2002)

Mechanistic studies on the formation of deoxyribonolactone by UV irradiation of hexamer d(GC1BrUGC)2 (ODN 2a) containing 1′-deuterio-2′-deoxyadenosine 1 was examined. The kinetic isotope effect (kH/kD) for the f

HETEROORGANIC FURAN DERIVATIVES. 61. TRIMETHYL(5-METHYL-2-FURYL)SILANE AND TRIMETHYL(5-METHYL-2-FURYL)GERMANE

Lukevits, E.,Ignatovich, L. M.,Iovel', I. G.,Gol'dberg, Yu. Sh.,Shimanskaya, M. V.

, p. 15 - 17 (1987)

The transformations of trimethyl(5-methyl-2-furyl)silane and trimethyl(5-methyl-2-furyl)germane were studied upon vapor-phase oxidation by atmospheric oxygen on a V-Mo-Ag-O catalyst.Under these conditions, trimethyl(5-formyl-2-furyl)silane and trimethyl(5-formyl-2-furyl)germane are formed albeit in only 5-7percent yield.This low yield is a consequence of the thermal instability of the starting compounds and the aldehydes formed.The oxidation of 2-methyl-5-tert-butylfuran was studied under comparable conditions.The corresponding aldehyde was obtained in 30percent yield.A scheme was proposed for the catalytic oxidation of 5-substituted 2-methylfurans.

A palladium catalyzed efficient synthesis of γ-methylene-α, β-unsaturated γ-lactones via cyclization of 3,4-alkadienoic acids

Ma, Shengming,Yu, Fei

, p. 9896 - 9901 (2005)

An efficient method was developed for the synthesis of γ-methylene- α,β-unsaturated γ-lactones from the Pd-catalyzed cyclization of 3,4-alkadienoic acids. Control experiment shows that the reaction should be carried out under a N2 atmosphere to ensure the high purity of the products.

-

Shaw

, p. 2510,2512 (1946)

-

Pd/C-Cu mediated direct and one-pot synthesis of γ-ylidene butenolides

Rambabu,Bhavani,Nalivela, Kumara Swamy,Mukherjee, Soumita,Rao, M.V. Basaveswara,Pal, Manojit

, p. 2151 - 2155 (2013)

10% Pd/C in combination with CuI, PPh3, and Et3N has been identified as an effective catalyst system for the coupling of (Z)-3-iodoacrylic acid with terminal alkynes in 1,4-dioxane leading to the one-pot synthesis of γ-ylidene butenolides. The methodology showed remarkable regio- and stereoselectivity as only the five-membered lactone ring products were formed with an exocyclic double bond possessing Z-geometry.

Intramolecular Photocycloaddition of 2(5 H)-Furanones to Temporarily Tethered Terminal Alkenes as a Stereoselective Source of Enantiomerically Pure Polyfunctionalyzed Cyclobutanes

Xin, Yangchun,Rodríguez-Santiago, Luís,Sodupe, Mariona,álvarez-Larena, Angel,Busqué, Félix,Alibés, Ramon

, p. 3188 - 3199 (2018)

Allyloxymethyloxymethyl and 4-pentenoyloxymethyl substituents have been used as tethering groups to study the intramolecular [2 + 2] photocycloaddition of chiral 5-substituted 2(5H)-furanones. The photoreactions proceed in good yield and provide the expected regio- and diastereoselective tricyclic compounds with complementary regioselectivity, which depends on whether the vinyl chain is attached to the furanone by an acetal or an ester linkage. Computational simulations agree with experimental observations and indicate that the origin of the different observed regioselectivity in the intramolecular photochemical reaction of lactones 5 and 6 arises from the relative stability of the initial conformers. The synthetic potential of the enantiomerically pure photoadducts is illustrated by preparing an all-cis 1,2,3-trisubstituted cyclobutane bearing fully orthogonally protected hydroxyl groups.

Efficacy and site specificity of hydrogen abstraction from DNA 2-deoxyribose by carbonate radicals

Roginskaya, Marina,Moore,Ampadu-Boateng,Razskazovskiy

, p. 1431 - 1437 (2015)

The carbonate radical anion CO3?- is a potent reactive oxygen species (ROS) produced in vivo through enzymatic one-electron oxidation of bicarbonate or, mostly, via the reaction of CO2 with peroxynitrite. Due to the vitally essential role of the carbon dioxide/bicarbonate buffer system in regulation of physiological pH, CO3?- is arguably one of the most important ROS in biological systems. So far, the studies of reactions of CO3?- with DNA have been focused on the pathways initiated by oxidation of guanines in DNA. In this study, low-molecular products of attack of CO3?- on the sugar-phosphate backbone in vitro were analyzed by reversed phase HPLC. The selectivity of damage in double-stranded DNA (dsDNA) was found to follow the same pattern C4′ > C1′ > C5′ for both CO3?- and the hydroxyl radical, though the relative contribution of the C1′ damage induced by CO3?- is substantially higher. In single-stranded DNA (ssDNA) oxidation at C1′ by CO3?- prevails over all other sugar damages. An approximately 2000-fold preference for 8-oxoguanine (8oxoG) formation over sugar damage found in our study identifies CO3?- primarily as a one-electron oxidant with fairly low reactivity toward the sugar-phosphate backbone.

THERMAL ANALYSIS OF 1-DEOXY-1-GLYCINO-D-FRUCTOSE AND 1-β-ALANINO-1-DEOXY-D-FRUCTOSE

Birch, Edward J.,Lelievre, John,Richards, Edward L.

, p. 263 - 272 (1980)

Aspects of the pyrolysis of 1-deoxy-1-glycino-D-fructose and 1-β-alanino-1-deoxy-D-fructose are reported.Thermal analysis and parallel chemical investigations demonstrate that formation of these Amadori compounds provides a low-energy route to the thermal degradation of their amino acid and sugar moieties.Furthermore, the pathway leads to the production of increased quantities of various aroma compounds as compared with controls.Pyrolysis of the 1-amino-1-deoxyketoses also produces the toxic compound protoanemonin; a degradation pathway leading to its formation is proposed.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 108-28-1